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22
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(a) Aoyagi T., Nagai M., Ogawa K., Kojima F., Okada M., Ikeda T., Hamada M., Takeuchi T. J. Antibiot. 44:1991;949-955
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(b) Nagai M., Ogawa K., Muraoka Y., Naganawa H., Aoyagi T., Takeuchi T. J. Antibiot. 44:1991;956-961
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Nagai, M.1
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Tsuda, M.1
Muraoka, Y.2
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Takeuchi, T.5
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25
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85031143171
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US Patent 5, 359, 138, 1994
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(d) Takeuchi, T.; Aoyagi, T.; Hamada, M.; Naganawa, H.; Ogawa, K.; Nagai, M.; Muraoka, Y.; Tsuda, M. US Patent 5, 359, 138, 1994.
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Takeuchi, T.1
Aoyagi, T.2
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Naganawa, H.4
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Nagai, M.6
Muraoka, Y.7
Tsuda, M.8
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26
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0029875108
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(e) Tsuda M., Muraoka Y., Nagai M., Aoyagi T., Takeuchi T. J. Antibiot. 49:1996;281-286
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Tsuda, M.1
Muraoka, Y.2
Nagai, M.3
Aoyagi, T.4
Takeuchi, T.5
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27
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0029949823
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(f) Tsuda M., Muraoka Y., Nagai M., Takeuchi T., Aoyagi T. J. Antibiot. 49:1996;287-291.
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Tsuda, M.1
Muraoka, Y.2
Nagai, M.3
Takeuchi, T.4
Aoyagi, T.5
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28
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85031144182
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The earlier general route to α-keto amides from carboxylic acids followed the sequence shown below
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The earlier general route to α-keto amides from carboxylic acids followed the sequence shown below.
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30
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85031131067
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9a formed most probably by the intramolecular addition of the free amino group to the nitrile (see Section 3.1.2)
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A side product in the deprotection of 8 was shown to be the pyrrolidin-3-one 9a formed most probably by the intramolecular addition of the free amino group to the nitrile (see Section 3.1.2).
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31
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85031133884
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The synthetic poststatin was identical in all respects to a sample kindly provided by Dr Y. Muraoka
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The synthetic poststatin was identical in all respects to a sample kindly provided by Dr Y. Muraoka.
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32
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0026523938
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(a) Toda S., Obi Y., Numata K.-., Hamagishi Y., Tomita K., Komiyama N., Kotake C., Furumai T., Oki T. J. Antibiot. 45:1992;1573-1579
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, vol.45
, pp. 1573-1579
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Toda, S.1
Obi, Y.2
Numata, K.-.3
Hamagishi, Y.4
Tomita, K.5
Komiyama, N.6
Kotake, C.7
Furumai, T.8
Oki, T.9
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33
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0026545767
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(b) Toda S., Kotake C., Tsuno T., Narita Y., Yamasaki T., Konishi M. J. Antibiot. 45:1992;1580-1586
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(1992)
J. Antibiot.
, vol.45
, pp. 1580-1586
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Toda, S.1
Kotake, C.2
Tsuno, T.3
Narita, Y.4
Yamasaki, T.5
Konishi, M.6
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34
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0027939892
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(c) Suzuki K., Toda S., Furumai T., Fukagawa Y., Oki T. J. Antibiot. 47:1994;982-991.
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(1994)
J. Antibiot.
, vol.47
, pp. 982-991
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Suzuki, K.1
Toda, S.2
Furumai, T.3
Fukagawa, Y.4
Oki, T.5
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36
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85031133811
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was prepared from 4-methyl-1-pentanol by oxidation to the corresponding aldehyde. Wittig olefination with (tert-butoxycarbonylmethylene)triphenylphosphorane afforded tert-butyl-(E)-6-methyl-2-heptenoate as a 95:5 mixture of geometric isomers. Deprotection with TFA followed by fractional distillation gave the isomerically pure (E)-acid
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(E)-6-Methyl-2-heptenoic acid ( 31 ) was prepared from 4-methyl-1-pentanol by oxidation to the corresponding aldehyde. Wittig olefination with (tert-butoxycarbonylmethylene)triphenylphosphorane afforded tert-butyl-(E)-6-methyl-2-heptenoate as a 95:5 mixture of geometric isomers. Deprotection with TFA followed by fractional distillation gave the isomerically pure (E)-acid 31.
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37
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85031137772
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13C NMR spectra of all intermediates. Additional evidence was obtained from a 1:1 mixture of 22 and its alanine epimer prepared by equilibration with triethylamine. Cyclization, according to the protocol shown in Scheme 6, furnished 29 and its alanine epimer in a ratio of 1:1. This control experiment demonstrated unambiguously that the stereochemistry of 29 was intact
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13C NMR spectra of all intermediates. Additional evidence was obtained from a 1:1 mixture of 22 and its alanine epimer prepared by equilibration with triethylamine. Cyclization, according to the protocol shown in Scheme 6, furnished 29 and its alanine epimer in a ratio of 1:1. This control experiment demonstrated unambiguously that the stereochemistry of 29 was intact.
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39
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0033588064
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and references therein
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Wasserman H.H., Xia M., Wang J., Petersen A.K., Jorgensen M. Tetrahedron Lett. 40:1999;6163-6166. and references therein.
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(1999)
Tetrahedron Lett.
, vol.40
, pp. 6163-6166
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Wasserman, H.H.1
Xia, M.2
Wang, J.3
Petersen, A.K.4
Jorgensen, M.5
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40
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85031135128
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We thank Dr Takaaki, Institute of Microbial Chemistry, Tokyo for samples of phebestin and probestin
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We thank Dr Takaaki, Institute of Microbial Chemistry, Tokyo for samples of phebestin and probestin.
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